Diverse synthesis of α-tertiary amines and tertiary alcohols via desymmetric reduction of malonic esters

Haichao Liu, Vincent Ho Man Lau, Pan Xu, Tsz Hin Chan and Zhongxing Huang ()
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Haichao Liu: The University of Hong Kong
Vincent Ho Man Lau: The University of Hong Kong
Pan Xu: The University of Hong Kong
Tsz Hin Chan: The University of Hong Kong
Zhongxing Huang: The University of Hong Kong

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Amines and alcohols with a fully substituted α-carbon are structures of great value in organic synthesis and drug discovery. While conventional methods towards these motifs often rely on enantioselective carbon-carbon or carbon-heteroatom bond formation reactions, a desymmetric method is developed here by selectively hydrosilylating one of the esters of easily accessible α-substituted α-amino- and -oxymalonic esters. The desymmetrization is enabled by a suite of dinuclear zinc catalysts with pipecolinol-derived tetradentate ligands and can accommodate a diverse panel of heteroatom substituents, including secondary amides, tertiary amines, and ethers of different sizes. The polyfunctionalized reduction products, in return, have provided expeditious approaches to enantioenriched nitrogen- and oxygen-containing molecules, including dipeptides, vitamin analogs, and natural metabolites.

Date: 2022
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DOI: 10.1038/s41467-022-32560-1

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